Upon leaving Dalhousie, Montgomery worked as a teacher in various island schools. Montgomery did not enjoy her teaching career, however, she was content because it afforded her time to write. Beginning in 1897, she began to have her short stories published in various magazines and newspapers. A prolific talent, Montgomery had over 100 stories published from 1897 to 1907 inclusive.

During her teaching years, Montgomery had numerous love interests. As a highly fashionable young woman, she enjoyed "slim, good looks," and she was the attention of several young men. In 1889, Montgomery began a relationship with a Cavendish boy named Nate Lockhart. To Montgomery, the relationship was merely a humorous and witty friendship. It ended abruptly when Montgomery refused his marriage proposal.

The early 1890s brought unwelcome advances from Mr. John A. Mustard and Will Pritchard. Mr. Mustard, her teacher, quickly became her suitor who tried to impress her with his knowledge of religious matters. His best topics of conversation were his thoughts on Predestination and "other dry points of theology." He held little appeal for Montgomery. During the period when Mustard’s interest became more pronounced, Montgomery "found a new interest" in Will Pritchard, the brother of her friend Laura Pritchard. This friendship was more amiable; however, again, Montgomery felt less than her suitor did for her. When Pritchard sought to take their friendship further, Montgomery resisted. Montgomery refused marriage proposals from both because the former was narrow-minded and latter was merely a good chum. She ended the period of flirtation when she moved to Prince Edward Island. However, she and Pritchard did keep up correspondence over six years until Pritchard caught influenza and died in 1897.

In 1897, Montgomery accepted the proposal of Ed Simpson, who was a student in French River near Cavendish. Montgomery wrote that she accepted his proposal out of a desire for "love and protection" and because she felt her prospects were rather low. While teaching in Lower Bedeque, she had a brief but passionate romantic attachment to Herman Leard, a member of the family with which she boarded. In 1898, after much unhappiness and disillusionment, Montgomery broke off her engagement to Simpson. Montgomery no longer sought romantic love.

In 1898, Montgomery moved back to Cavendish to live with her widowed grandmother. For a short time in 1901 and 1902, she worked in Halifax for the newspapers Chronicle and Echo. She returned to live with and care for her grandmother in 1902. Montgomery was inspired to write her first books during this time on Prince Edward Island. Over the next thirteen years, Montgomery stayed in Cavendish to take care of her grandmother. This coincided with period of considerable income from her publications. Although she enjoyed this income, she was aware that “marriage was a necessary choice for women in Canada.”

In 1908, Montgomery published her first book, Anne of Green Gables. Three years later, shortly after her grandmother's death, she married Ewan (found in Montgomery's notes and letters as "Ewan") Macdonald (1870—1943), a Presbyterian Minister, and they moved to Ontario where he had taken the position of minister of St. Paul's Presbyterian Church, Leaskdale in present-day Uxbridge Township, also affiliated with the congregation in nearby Zephyr. They had three sons, the second of whom was stillborn. The great increase of her writings in Leaskdale is the result of her need to escape the hardships of real life. Montgomery underwent several periods of depression while trying to cope with the duties of motherhood and church life and with her husband’s attacks of religious melancholia and deteriorating health: "For a women who had given the world so much joy was mostly an unhappy one." For much of her life, writing was her one great solace. Also, during this time, Montgomery was engaged in a series of "acrimonious, expensive and trying lawsuits with the publisher L.C. Page, which dragged on until she finally won in 1929."

Montgomery wrote her next eleven books from the Leaskdale manse. The structure was subsequently sold by the congregation and is now the Lucy Maud Montgomery Leaskdale Manse Museum. In 1926, the family moved in to the Norval Presbyterian Charge, in present-day Halton Hills, Ontario, where today the Lucy Maud Montgomery Memorial Garden can be seen from Highway 7.

In 1935, upon her husband's retirement, Montgomery moved to Swansea, Ontario, a suburb of Toronto, buying a house which she named Journey's End, situated on the Humber River. Montgomery continued to write, publishing Anne of Windy Poplars in 1936, Jane of Lantern Hill in 1937, and Anne of Ingleside in 1939.

In the last year of her life, Montgomery completed what she intended to be a ninth book featuring Anne, titled The Blythes Are Quoted. It included fifteen short stories (many of which were previously published) that she revised to include Anne and her family as mainly peripheral characters; forty-one poems (most of which were previously published) that she attributed to Anne and to her son Walter, who died as a soldier in the Great War; and vignettes featuring the Blythe family members discussing the poems. An abridged version, which shortened and reorganized the stories and omitted all the vignettes and all but one of the poems, was published as a collection of short stories The Road to Yesterday in 1974. A complete edition of The Blythes Are Quoted, edited by Benjamin Lefebvre, was published in its entirety by Viking Canada in October 2009.

Death and legacy

It was reported that Montgomery died of congestive heart failure in Toronto.Selected Journals of L.M. Montgomery Volume V: 1935-1942 p. 399 The primary cause of death on her certificate was "Coronary Thrombosis." However, it was revealed by her granddaughter, Kate Macdonald Butler, in September 2008 that Montgomery suffered from depression - possibly as a result of caring for her mentally-ill husband for decades - and took her own life via a drug overdose. But, there is another point of view. According to Mary Rubio, who wrote a biography of Montgomery Lucy Maud Montgomery: The Gift of Wings (2008), the message was intended to be a journal entry rather than a suicide note.

She was buried at the Cavendish Community Cemetery in Cavendish following her wake in the Green Gables farmhouse and funeral in the local Presbyterian church.

During her lifetime, Montgomery published 20 novels, over 500 short stories, an autobiography, and a book of poetry. Aware of her fame, by 1920 Montgomery began editing and recopying her journals, presenting her life as she wanted it remembered. In doing so certain episodes were changed or omitted.Her major collections are archived at the University of Guelph, while the L.M. Montgomery Institute at the University of Prince Edward Island coordinates most of the research and conferences surrounding her work. The first biography of Montgomery was The Wheel of Things: A Biography of L.M. Montgomery, (1975) written by Mollie Gillen. Dr. Gillen also discovered over 40 of Montgomery's letters to her pen-friend George Boyd MacMillan in Scotland and used them as the basis for her work. Beginning in the 1980s, her complete journals, edited by Mary Rubio and Elizabeth Waterston, were published by the Oxford University Press. From 1988-95, editor Rea Wilmshurst collected and published numerous short stories by Montgomery.

Despite the fact that Montgomery published over twenty books, "she never felt she achieved her one 'great' book." Her readership, however, has always found her characters and stories to be among the best in fiction. Mark Twain said Montgomery’s Anne was “the dearest and most moving and delightful child since the immortal Alice. Montgomery was honoured by being the first female in Canada to be named a fellow of the Royal Society of Arts in England and by being invested in the Order of the British Empire in 1935.

Her fame was not limited to Canadian audiences. Anne of Green Gables became a huge success in Japan. Every year, thousands of Japanese tourists "make a pilgrimage to a green-gabled Victorian farmhouse in the town of Cavendish on Prince Edward Island...." A national park was established near her home in Cavendish in honour of her works. Montgomery is one of Canada’s best-known authors and continues to be a source of pride for Canadians.

Novels

• Anne of Green Gables (1908)
• Anne of Avonlea (1909) (sequel to Anne of Green Gables)
• Kilmeny of the Orchard (1910)
• The Story Girl (1911)
• The Golden Road (1913) (sequel to The Story Girl)
• Anne of the Island (1915) (sequel to Anne of Avonlea)
• Anne's House of Dreams (1917) (sequel to Anne of Windy Poplars)
• Rainbow Valley (1919) (sequel to Anne of Ingleside)
• Rilla of Ingleside (1921) (sequel to Rainbow Valley)
• Emily of New Moon (1923)
• Emily Climbs (1925) (sequel to Emily of New Moon)
• The Blue Castle (1926)
• Emily's Quest (1927) (sequel to Emily Climbs)
• Magic for Marigold (1929)
• A Tangled Web (1931)
• Pat of Silver Bush (1933)
• Mistress Pat (1935) (sequel to Pat of Silver Bush)
• Anne of Windy Poplars (1936) (sequel to Anne of the Island)
• Jane of Lantern Hill (1937)
• Anne of Ingleside (1939) (sequel to Anne's House of Dreams)
• The Blythes Are Quoted, edited by Benjamin Lefebvre (2009) (sequel to Rilla of Ingleside)

Short story collections

• Chronicles of Avonlea (1912)
• Further Chronicles of Avonlea (1920)
• The Road to Yesterday (1974)
• The Doctor's Sweetheart, selected by Catherine McLay (1979)
• Akin to Anne: Tales of Other Orphans, edited by Rea Wilmshurst (1988)
• Along the Shore: Tales by the Sea, edited by Rea Wilmshurst (1989)
• Among the Shadows: Tales from the Darker Side, edited by Rea Wilmshurst (1990)
• After Many Days: Tales of Time Passed, edited by Rea Wilmshurst (1991)
• Against the Odds: Tales of Achievement, edited by Rea Wilmshurst (1993)
• At the Altar: Matrimonial Tales, edited by Rea Wilmshurst (1994)
• Across the Miles: Tales of Correspondence, edited by Rea Wilmshurst (1995)
• Christmas with Anne and Other Holiday Stories, edited by Rea Wilmshurst (1995)

Short stories by chronological order

• Lucy Maud Montgomery Short Stories: 1896 to 1901 (2008) ISBN 978-1406565102
• Lucy Maud Montgomery Short Stories: 1902 to 1903 (2008) ISBN 978-1406565119
• Lucy Maud Montgomery Short Stories: 1904 (2008) ISBN 978-1406565126
• Lucy Maud Montgomery Short Stories: 1905 to 1906 (2008) ISBN 978-1406565133
• Lucy Maud Montgomery Short Stories: 1907 to 1908 (2008) ISBN 978-1406565140
• Lucy Maud Montgomery Short Stories: 1909 to 1922 (2008) ISBN 978-1406565157

Poetry

• The Watchman & Other Poems (1916)
• The Poetry of Lucy Maud Montgomery, selected by John Ferns and Kevin McCabe (1987)

Non-fiction

• Courageous Women (1934) (with Marian Keith and Mabel Burns McKinley)

Autobiography

• The Story of My Career (1975; originally published in Everywoman's World in 1917)
• The Selected Journals of L.M. Montgomery (5 vols.), edited by Mary Rubio and Elizabeth Waterston (1985—2004)

Texts, images and collections

• Works by L M Montgomery at Project Gutenberg Australia
• Picturing A Canadian Life: L.M. Montgomery's Personal Scrapbooks and Book Covers
• L.M. Montgomery Collection at the University of Guelph Library, Archival and Special Collections, contains her personal journals, scrapbooks, and more than 800 items
• CBC Digital Archives - Beyond Green Gables: The Life of Lucy Maud Montgomery
• Representative Poetry Online
• Lucy Maud Montgomery's contract for Anne of Green Gables, 1907
• Anne of Green Gables Centenary - This site includes information about the centenary anniversary of Lucy Maud Montgomery’s Anne of Green Gables.

Audiobook

• LibriVox (free audiobooks of public domain)

Organizations

• L.M. Montgomery Institute
• L.M. Montgomery Research Centre Highlights the extensive L.M. Montgomery collection at the University of Guelph Library Archival & Special Collections.
• Lucy Maud Montgomery Leaskdale Manse Museum Website
• The L.M. Montgomery Research Group is a site that includes a blog, an extensive bibliography of reference materials, and a complete filmography of all adaptations of Montgomery texts.
• The L.M. Montgomery Literary Society is a site that includes information about Montgomery and research from the newsletter The Shining Scroll. Read articles about Montgomery and World War I, her book dedications, tour her PEI sites, learn about her connections to Japan and more.

Other information

• Little More Montgomery has information on the author's life in Ontario

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